An early autumn trip to this 3,147-acre park on the Chesapeake Bay’s eastern shore delivers sweet shoreline camping without the swarming summertime mosquitoes. But the bay can get rough any time of year, so be sure to waterproof your sleeping bag and key gear (we like the Outdoor Research Lateral Dry Bag; $39 to $69; outdoorresearch.com). From the park’s marina, paddle 3.6 miles south, into the Little Annemessex River (rent a kayak or canoe for $50/day; see park contact below). Follow brown water-trail signs past uninhabited coastal wetlands to your backcountry target: a tent platform on Long Point, a sandy six-acre spit of land cut off from the southeastern corner of the main island by a thin canal. The short trip is easy to extend—scope for nesting herons in the many waterways that permeate the island’s salt marshes or drop a bait line for peak-season blue crabs (see below; $10 license required; dnr.maryland.gov). To return, retrace your route, or continue west past long stretches of sandbars and beaches while circumnavigating the island’s 13-mile coastline. Permit Reservations required for camping; $8

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Perfect Days

Mobile, ALPine Creek Trail

On this mellow 3.7-mile lollipop loop, scrub pine gives way first to lush wetlands, then the famous white sands of the Gulf shore—where you can swim, snorkel, and spot endangered loggerhead sea turtles. Afterward, explore more of inland Alabama via horseback during a one-hour guided ride at Oak Hollow Farm ($30/person; oakhollowfarm.net). Trip ID34995

Providence, RIBlock Island

Visiting all of Block Island, 13 miles off the coast, is a triathlon of sorts: First, catch the high-speed ferry from Newport ($17 round-trip; blockislandferry.com). Next, rent a bike ($30; bimopeds.com) to explore the island’s glacier-carved geology on your way to the trailhead, 2.8 miles away at Rodman’s Hollow. From there, a 3.5-mile (round-trip) hike passes blackberry bushes en route to oceanside bluffs. Trip ID278848

Roanoke, VATinker Cliffs

This 6.6-mile out-and-back ascends almost 1,700 feet on the Andy Layne Trail before leveling out as it joins the AT, where the 60-foot Tinker Cliffs offer views across the Catawba Valley clear to McAfee Knob. On your way home, stop in Catawba for all-you-can-eat fried chicken and Southern-style sides at the Homeplace Restaurant (get there by mid-afternoon to beat the long lines; on.fb.me/thehomeplace). Trip ID525894

Explore: Boston-Area Hikes

Skyline Trail Loop, Blue Hills Reservation

Get sweeping views of the city from the summit of 635-foot Great Blue Hill—the tallest Atlantic Coast peak south of Maine. This six-mile figure-eight takes you past ponds and through dense hardwoods. (Trip ID 431589). Download our free smartphone app, GPS Trails, to check out a dozen more hikes within the metro area. Get it at backpacker.com/gpstrails.

Hike For Heroes

Give a salute atop New Hampshire’s highest peaks.

Three days after the terrorist attacks of September 11, 2001, six somber hikers summited New Hampshire’s 4,459-foot Mt. Liberty and erected a U.S. flag on a makeshift pole, in tribute to the victims. The patriotic act went viral, and a tradition was born.

Every September since, groups of hikers carry flags to the state’s 48 summits reaching 4,000 feet and above, from Mts. Adams to Zealand, and fly the colors for two hours in remembrance (flags from other countries are welcome as well). “It’s our way as hikers to show that hope and understanding are possible,” says founding hiker Jim Roy.

Bag an easier peak like 4,052-foot Mt. Jackson via the 3.1-mile (one-way) Webster Cliff route (Trip ID 1736083), or if you prefer longer miles and rougher terrain, target the routes up Mt. Isolation (Trip ID 534226) or Allen Mountain. Even non-hikers can participate, via ski lifts or auto roads. Get in on the chest-swelling event this year on September 8; find registration info and hike details at flagsonthe48.org.

Your region's go-now guide: Visit a new hikers' hostel connected to 50 miles of trail in Maine's Bigelow Mountains, see the rare Oconee bell in South Carolina's Jocassee Gorges area, explore the world's longest mapped cave system near Louisville, and more.

Your region's go-now guide: Take in Pennsylvania's nighttime skies in the Cherry Springs State Park, ascend the 2,625-foot Mt. Moosalamoo in Vermont, enjoy the new 38-mile section of the Cumberland Trail in Tennessee, and more.